Guide To Chicago’s ‘Lady In Red’ Lipstick

Red Lipstcik Guide

Photo: Our own Lady In Red-Author, Helen Marshall


First, ladies, we confess we are making the assumption that you are the type of woman who can boldly go out in public wearing bright red lipstick.

It’s not for everyone. It is for those who stand tall. It is for those who declare “I am here.” Regardless of age.

A Shrinking Violet does not wear red lipstick.

So, Miss Tiger Lily, here’s how to wear red so you don’t look like Faded Rose.


There’s a red that’s right for you no matter your hair color or skin tone. Most people look best in a bluish red or a pure red. Orange-y reds can make your teeth look yellow.

Try some different colors on your lips. Take a photo of yourself wearing the color or have a friend take one. A photo gives you a more accurate view of how the color appears than does your reflection in a mirror.

If you are 40-plus, go for a bright red or light red. The dark reds add years.


A perfect application is key. Messy red lipstick is not ladylike.

Perhaps your hotness could melt steel but you still must look like a lady if wearing red lipstick. Sloppy red lipstick makes you look clownish and like—umm—not a lady.

Perfect application is all the more important if you are of a certain age.

Radiating lines—called perioral lines–form around our mouths from years of eating, smiling, puckering and talking. Smokers are notorious for getting them from the act of drawing on a cigarette. (Quit now!)

Your lipstick wants to migrate into those lines.

This guide includes advice on how to prevent the bleeding and feathering of lipstick that makes a lady appear to be that sad, lonely and desperate creature sitting by herself at a bar.


Here are the supplies you will need to achieve a full-on tricked-out red mouth:

• Red lipstick (obviously)
• Red lipstick in a color lighter and/or brighter than the main red
• Clear wax pencil or a “pore filler” product
• Red lip pencil, same color as your lipstick
• Dark flesh tone lip pencil
• Pearly highlighting fluid
• Royal blue eye pencil
• A cotton swab
• A magnifying mirror


Learning a few terms will help you better visualize the application.

Vermilion Ridge: The invisible line separating the reddish skin of the lips from the surrounding “flesh tone” skin of the face. In some individuals, the difference in appearance is more pronounced, while in others the two skin types and colors seem almost to blend.

Philtrum: Sometimes called the Angel’s Kiss, it is the groove-like indentation often found below the nose and above the upper lip.


First, exfoliate your lips by washing them gently with a nubbly washcloth to remove any dead skin.

Now, here’s the critical step to prevent feathering. Feathering occurs when lipstick bleeds into the furrow-like perioral lines that radiate from your mouth.

If you’re Sweet 16, you may have no such lines. Lucky you! If you’re a Boomer Babe, read on.

The idea is to create a physical dam to keep the lipstick from migrating. Several companies make clear wax pencils for this purpose. “Pore filler” products work too. So do some lip balms providing they are waxy and have very little emollient.

Draw the clear wax pencil around your mouth outside the vermilion ridge, on the flesh tone portion of your skin. Pat to blend and help the product settle into your lines.


Lips lose volume and appear thinner as a person ages. Here are some tips to add definition and make your lips look fuller. Use a magnifying mirror.

1. Use the dark flesh tone lip pencil to draw a short horizontal line below the center of your lower lip. Apply it on the flesh colored area, not on the vermilion portion. Smudge gently. This creates a subtle shadow.

2. Highlight the area above the center third of your upper lip with a bit of pearly highlighter fluid. Or, dab it on the philtrum only. Blend. This adds definition and, again, makes the lips appear fuller by adding reflective brightness.

3. Now, add blue. It sounds insane but it works. Use the blue eye pencil to create a bluish shadow at the corners of your mouth. This adds more definition, makes the corners appear deeper and the lips appear fuller. Open wide and dry the inside of the corners of the mouth with the cotton swab. Use the blue pencil to lightly color just inside the corners of the mouth. Make sure there is no blue color on the “flesh tone” skin of your face.


Hah, you thought we’d never get around to applying actual lipstick!

1. Sharpen your red lip pencil and use it to outline the upper and lower lip. The pencil should be the same color—more or less—as your lipstick. You want to apply it right on top of the vermilion ridge or just barely outside it. Try drawing your line from the outer corner of your mouth, along the ridge toward the center for better control of the pencil.

2. Use the flat edge of the pencil to lightly fill in your entire lip, top and bottom.

3. Now, apply your red lipstick to your upper and lower lips directly from the tube.

4. To make the lower lip “pop”, apply a lighter or brighter red to the center of the lower lip.


Avoid a lipstick-on-your-teeth “oops” by placing your (clean) index finger in your mouth. Close your lips around your finger and draw the finger out of your mouth. The lipstick that sticks to the finger is the color that would have ended up on our teeth.

Now, don’t eat or drink! Just kidding, sort of. The oils in food and the act of biting and chewing will disturb your lipstick. You may gently sip a drink but do so by placing the glass against your lip and tipping the beverage into your mouth. If you’re wearing your lipstick to a dinner date, order something that you can cut into pieces and place directly into your mouth without dragging the food across your lips. Say no to: ribs, hamburgers, spaghetti and oily salad dressings.

Now, go out there and knock ‘em dead.

  • C. Baesemann

    This is great! I love the detailed instructions and the author looks FABOO!

  • Penny Cagney

    At last I know how to do this! Thank you, thank you, Ms. Marshall!

  • M Black

    Rah, rah, RED!

  • Denise S.

    I especially like the anatomy lesson!

  • Susan B.

    Foolproof and funny! Thank you, Lady In Red, for setting us straight and helping us avoid looking older and clown-like! Can you tackle dark circles next?

  • Trixie

    OK – the navy lip pencil trick is a new one, but I’ll try it. I used to have this awesome Paloma Picasso red. Wonder if she still makes it?

  • Susan Peckitt

    I suppose a kiss would ruin everything.

  • Patrice in Paris

    Wow. Do you really have time to do this in the morning? or do you reserve red for only special occasions? You shud put together and market a red lip packet for those of us who cant be bothered to go out and shop for all the separate items here! Thanks for the tips on the radiating lines. Getting older does present new challenges.. I find that my best reds are a plummy-tnaish colr that isnt too far off my own skin tone. of course this has no where near the WOW factor that good ol MAx Factor had in mind when he was making up all thos emovie stars!

  • Jenne

    Helen is an expert ..and I mean expert. She has been a red lipstick afficianado since we were in college together

  • Christine

    Red is timeless and classy—my mom always said my white Slicker lipstick from Yardley (circa 1967) was “tacky”!!! Her most recent favorite red was “Marilyn” by Chanel. Thanks helen!

  • Dianne

    Never realized it was so complicated. I think I’ll stick with Raspberry Glace.

  • Suki

    Whew! and good grief. And the worst of it is, I’ll probably start using some of your tips. Having had professional makeup done once for a publicity photo (it took 3 hours), I can appreciate the effects of doing it right. Thanks, Krizzer

  • bonniebuck

    Yes, the dark blue does sound insane.

  • Julia

    Great piece! The sunglasses are a must with red lipstick.

  • Sue Hufford

    Now I remember some of these tips and terminology from our live demo makeup lesson last year. Thank you for sharing, and for helping us Boomer Babes to stay beautiful!

  • Liz R.

    Great article that gives a thorough how-to on achieving that woman in red lipstick look! I picked up some new techniques!

  • Joan

    Love the instructions, but I might need private lessons to master this. I’ve never even attempted red!

  • Penelope Cagney©

    How about a YouTube instruction video, Ms. Kriz?

  • Sofia

    Used to wear red on and of in my twenties and thirties. Then I chickened out. I just may try being more bold again. Thanks Helen

  • Beth Weiss

    Never knew there were so many steps to the process. Thanks for the info! Beth W.

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